Hit the Beach

While Maine's epically scenic coast is often noted for its craggy, rock-strewn shores, Kennebunkport has been gifted with multiple stretches of soft, white sand. Surfers flock to Goose Rocks Beach (pictured), a nearly 3-mile stretch of shore. You'll find families relaxing in beach chairs and on blankets under umbrellas. Another excellent stretch of Kennebunkport coast is found at Gooch's Beach, a striking swath of sand filled with sunbathers, beachcombers, families and swimmers.

Hop Aboard the Intown Trolley Tour

Learn the lay of Kennebunkport's land (and give your legs a break) aboard the informative Intown Trolley Tour. These trolleys have been rolling through Kennebunkport for more than 30 years, and point out the town's major sights to visitors, including the Bush compound, a local Franciscan monastery, and the so-called "spouting rock" along the coast. Tours also include colorful commentary highlighting the town's history.

Schooner Eleanor Boat Cruise

You'll be forgiven for romanticizing the seafaring history of southern Maine. The dreamy tales you envision become reality aboard the Schooner Eleanor, a contemporary boat built to the specifications of a traditional gaff rigged schooner, complete with spruce poles, mahogany surfaces and hand-carved boards. Hop aboard for a two-hour sail around the region's craggy shores, admiring a new perspective of Kennebunkport.

Explore the Lighthouses

Make like a professional photographer and snap classic shots of the looming lighthouses that rise above Maine's rocky coast. Five lights can be found within a 20-mile radius of Kennebunkport. Drive to Cape Porpoise to see the Goat Island Light, and take time to explore the Wood Island Light, Nubble Light (pictured), Whaleback Light and Boon Island Light. Be warned: not all the lights can be directly accessed, but they are visible from the road and offer ample photo opps.

Explore Dock Square

The heart of Kennebunkport, Dock Square is filled with boutiques, book stores, artisan ice cream parlors and candy shops. Spend an afternoon strolling the tiny town center, which is chock full of high-end retailers, bric-a-brac stores, restaurants and more. It's here that you'll also find a hub for boat tours and whale watching trips. Make sure to indulge in a lobster roll at The Clam Shack before leaving -- though don't arrive hungry; lines can be long.

Kennebunkport Food and Wine Festival

Foodies in the know flock to the multi-day Kennebunkport Food and Wine Festival held each June. See and be seen alongside the festival's well-heeled visitors at tasting events that include the Pop the Kennebunks gala party, Art of Dining dinners prepared by acclaimed chefs in exquisite local homes and a Grand Tapas party featuring small plates prepared by award-winning chefs. Tickets to the festival's events sell out well in advance; play it smart and book well in advance.

Shop at the Kittery Outlets

On a rainy day in Kennebunkport (and let's face it, this is Maine -- there's gonna be a rainy day), take the short drive from Kennebunkport and exercise your wallet at the Kittery Outlets. You'll find all manner of goods here, from sportswear at Eddie Bauer and lululemon to new kicks at Adidas and Under Armour outlets, and even high-end kitchenware at Le Creuset. Be a smart shopper: check the Kittery Outlets website before shopping to find coupons and discounts for many shops.

The Eastern Trail

Bring your bicycles to Kennebunkport or rent them in town and explore the 65-mile Eastern Trail, a stretch of the East Coast Greenway that connects Kittery to Casco Bay. The trail includes idyllic country roads, as well as off-road trails and is perfect for cyclists of all ages and skill levels. A new 6.2-mile portion of the trail can be easily accessed from town, connecting Kennebunk with the towns of Arundel and Biddeford.

Charter a Fishing or Lobster Boat Tour

With a shipbuilding and seafaring history that dates back to the 17th century, Kennebunkport is a logical jumping-off point for hitting the open sea. Bait your hook and line and book a fishing charter with Striker Charters, which offers inshore and offshore charters (trips target mackerel, herring, bluefin tuna and mako). Kids (and grownups!) will love a trip with Rugosa Lobster Tours aboard a classic, wooden, New England lobster boat. Watch your crew haul lobster traps, and even get up close and personal with the catch.

Pamper Yourself in the Trees

If your muscles have grown sore from beach walks and bicycling, or you simply want to treat yourself to extreme pampering, book a treatment at the Tree Spa at Hidden Pond. Literally tucked into the treetops 8 feet above the ground, three private treatment rooms are connected by a wooden boardwalk, completing the spa's Swiss Family Robinson-gone-luxe appeal. Let your aches and cares disintegrate during a Muscle Melt Massage or Herbal Garden Body Exfoliation.